Abstract
Stille cross coupling protocols were utilized for the synthesis of 3-(biaryl)-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl esters, which furnished products in high yields where in some cases Suzuki coupling under the conditions utilized provided complex reaction mixture. Samarium iodide reduction of the resulting coupling products produced both of the 2β-carbomethoxy-3-biaryl-8-oxabicyclo[3.2.1]octane diastereomers and the 2α-carbomethoxy-3-biaryl-8-oxabicyclo[3.2.1]octane diastereomers. Among the series synthesized, the benzothiophene substituted compounds demonstrated significant binding profiles of inhibition of WIN 35,438 with 177-fold selectivity for DAT versus SERT.
Copyright © 2012 Elsevier Ltd. All rights reserved.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Bridged Bicyclo Compounds / chemistry*
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Carboxylic Acids / chemistry*
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Cocaine / analogs & derivatives
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Cocaine / pharmacology
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Dopamine Plasma Membrane Transport Proteins / antagonists & inhibitors
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Dopamine Plasma Membrane Transport Proteins / metabolism
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Dopamine Uptake Inhibitors / chemical synthesis*
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Dopamine Uptake Inhibitors / chemistry
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Dopamine Uptake Inhibitors / pharmacology*
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Esters / chemical synthesis
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Esters / chemistry
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Esters / pharmacology*
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Humans
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Molecular Structure
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Selective Serotonin Reuptake Inhibitors / chemical synthesis*
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Selective Serotonin Reuptake Inhibitors / chemistry
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Selective Serotonin Reuptake Inhibitors / pharmacology*
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Serotonin Plasma Membrane Transport Proteins / metabolism
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Structure-Activity Relationship
Substances
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Bridged Bicyclo Compounds
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Carboxylic Acids
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Dopamine Plasma Membrane Transport Proteins
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Dopamine Uptake Inhibitors
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Esters
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Serotonin Plasma Membrane Transport Proteins
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Serotonin Uptake Inhibitors
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(1R-(exo,exo))-3-(4-fluorophenyl)-8-methyl-8- azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester
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Cocaine